Asymmetric Total Synthesis and Structural Reassignment of Nervione
Kunita Phakdeeyothin, Jian-Liang Li, Yi-Tian Hong, Rong-Jie Chein
TL;DR
This paper describes the complete synthesis of a natural compound called nervione and corrects its molecular structure based on new evidence.
Contribution
The paper provides the first asymmetric total synthesis of nervione and corrects its absolute configuration.
Findings
Nervione was synthesized in 10 steps from resorcinol using ortho-directed strategies and a key diastereoselective reduction.
Circular dichroism (CD) spectra discrepancies led to the reassignment of nervione’s absolute configuration to (3R, 8S).
Abstract
We report the asymmetric total synthesis of optically active nervione in both (+) and (−) forms, a natural product initially isolated from Nervilia concolor in 2022. Beginning with commercially available resorcinol, optically pure nervione was synthesized in 10 steps, employing a combination of ortho-directed strategies and a crucial late-stage, Lewis acid-mediated, highly diastereoselective reduction. Discrepancies observed in circular dichroism (CD) spectra prompted the reassignment of nervione’s absolute configuration from (3S, 8R) to (3R, 8S).
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Taxonomy
TopicsChemical synthesis and alkaloids · Marine Sponges and Natural Products · Phytochemistry and Bioactivity Studies